tagGay MaleUnderwear Friends Ch. 02

Underwear Friends Ch. 02


I couldn't stop thinking about my encounter with Mark. I was pretty sure I still liked girls, but I was so hot for Mark! I longed to kiss him, undress him, stroke his cock and slide it in my mouth again. And have him do the same for me.

I got to see him four days a week in gym class, and loved watching him strip to his boxers and A-shirts. The rest of the guys in class, including me, wore tighty-whitey briefs and colored t-shirts, but Mark transferred here from Dallas, and all the guys there wore white boxers with little patterns and white A-shirts. During our encounter last week, Mark let me try on his underwear, and I liked them so much, I was determined to switch myself.

Every year for Christmas, along with our other presents, my mom would always buy my little brother and me new underwear, white briefs from JCPenney. My dad always got a pack of boxer shorts, but I never really thought about them before. I never saw him in his underwear, and besides, men wore boxers, boys wore briefs. However, now that I was eighteen and a senior, I could start dressing more like a man.

My mom was fixing dinner, and I was setting the table. "Mom, are you planning on getting us underwear for Christmas again?"

"Huh? I guess I was thinking of that again. Why, do you want something special?"

"Yeah. I was thinking of trying boxer shorts and A-shirts. Some of the guys in gym class are switching to them. They seem more for older guys."

My mom laughed. "Well, I guess I didn't think of that before, but sure, I suppose I could pick some up for you. Do you want to pick them out with me?"

Be seen shopping for underwear with my mom? "No, that's okay, surprise me. The guys are wearing white boxers with little patterns. I'm not sure where their moms get them from. You can probably try Penney's. I'd also like to try some A-shirts if you can find some."

"I'll see what I can do."

"Thanks, Mom."

I started imagining what kinds of shorts she would get. Mark had shown me his underwear drawer, and he had a lot of variety.

The next day at school, Mark asked me if I wanted to help him with his algebra again. He winked at me and smiled, and I flashed a big smile back. "I'd love to."

As we walked to his house after school, I told him how I asked my mom to get me some boxers too.

"Cool, man! You looked so good wearing my boxers. I can't wait to see you wearing some new ones. I hope I don't get a hard-on watching you undress in the locker room."

"Now you know what I have to avoid when I see you undress!"

We got to his house, and as usual, his mom was working. We had about three hours.

"You want to wear my underwear while we work again?"

"You bet! Pick me out something hot, and I'll call my mom to let her know I'll be late."

I set out our math books, and Mark came back with a pair of white boxers with little blue diamonds and an A-shirt for me. I undressed and slipped on the clothes he gave me, while Mark striped down to his yellow boxers and A-shirt. We checked each other out and smiled. Mark kissed me, and we sat down to do homework.

Mark kept sliding his hand to the tent in my shorts, and I pushed him away. "Man, we'll never get this done if we start that now. Tell you what - you finish your assignment and I'll check it over. If you get 80% right, I'll give you a 'B' for 'blowjob'. How's that?"

Mark laughed, "Wow, that's incentive! If I had that offer before, I'd be a math genius by now!"

We worked on our homework. I helped Mark out with a few questions, and soon he was done. I checked over his work - 13 right out of 15 - 87%. "You pass! Now, let's give you your reward."

Mark slid his chair back from the table, and I kneeled down in front of him. I opened the fly in his yellow boxers and pulled his hard cock out. "Mmmm, somebody looks good enough to eat!"

I gently kissed his soft cockhead and ran my tongue around the rim. Mark moaned in delight. I slid my hand around the shaft, and slid his cock in my mouth. I lightly sucked on his throbbing member, as I jacked it in and out of my mouth. I wanted to please him so badly, and I loved hearing his little moans of delight. It was so sexy sucking him off in his shorts, and before he knew he, he yelled 'I'm cumming!", and he shot his load in my mouth.

I gulped as I tried to contain the cum explosion. He was so warm and salty. I licked off thick strings of his wad from his cock, smacking my lips as I swallowed them. His cock clean and getting limp, I moved up to sit on his lap and kiss Mark's soft lips. He slid his tongue in my mouth, eager to taste some of his cum on my lips. We kissed for some time, exploring each other's mouths, until my throbbing cock was poking him in the belly, and he laughed, "Your turn".

We switched places, me sitting on his kitchen chair, and Mark kneeling at my feet. He pulled my hard cock out of the fly of the boxers, and slid the whole length down his throat. Mark bobbed his head back and forth, my cock sliding all the way in and out of his mouth. I placed my hands on his head, and gently caressed his hair as I guided him. I was so aroused, sitting there in Mark's boxers with the little blue diamonds, as I watched my cock disappear in his warm mouth. In no time, I felt my balls quivering, and I shot a huge load in his mouth, Mark gagging as he swallowed my seed. I saw some dribble out of his mouth.

Mark pulled away, and I guided his face to mine, licking my cum off his chin and kissing those sticky lips. He sat on my lap, and we made out as before, kissing and caressing.

We stood up to get dressed before Mark's mom got home. I handed him back his underwear and put on my briefs.

"Man, I never knew underwear could get me so horny! My dad wears boxers and I never thought they were sexy until I met you."

"Your dad wears boxers? Cool! What kind?"

"I guess mostly white, I really don't know. Once in a while I see them in the laundry hamper."

"I think men's big boxers are so hot!"

"I'll see if I can sneak a pair of them over here to show you."

"Oh man, that would be great!"

Mark and I both had part-time jobs, so we only had one night a week where we were both off. We decided to make it a regular 'tutoring' session.

The next week, I snuck into my parent's room, and checked out my dad's underwear drawer. As I thought, he had mostly white boxers, but I also saw a pair of light blue ones and a white pair with hearts on them. I didn't think he would miss a pair of the white ones, so I grabbed one from the bottom of the pile and slipped it in my backpack. I would show them to Mark after school that day.

As we walked to Mark's house, I told him I brought him a surprise. "Your dad's boxers? Wow, I can't wait to see them!"

We unloaded our stuff on the table, and Mark said, "I don't have any homework tonight. Can I see your dad's shorts now?"

I laughed, "Easy, big fella!" I reached into the bottom of my backpack and pulled our a bag. I took out the shorts, they were large full-cut white boxers with snaps in the front. They looked a few sizes bigger than what Mark wore.

"Can I try them on?"

"Sure, model them for me."

Mark stripped down right there, and slipped on my dad's boxers. They hung very loose on him, and he instantly got an erection that made a tent.

"I feel like an real man in these. Wanna play a game? You can be my son."

"Sure, okay."

"Let's go to my room."

Mark sat in his bed, his cock poking a tent in the big white boxers. "Ray, get in here! The school just called, and you're failing English! They said you've been skipping class! I'm very disappointed with you. You need to be punished!"

I laughed, "Man, this game doesn't look very fun to me. Who wants to fail English?"

"Just play along, it will be fun."


"Get over here and take off your jeans. You're going to get a spanking!"

I thought it was a little weird, but what the hell. "Yes, sir." I took off my shirt and jeans and walked over in just my little white briefs.

"Lay across my lap. You need to learn a lesson, son."

I laid across Mark's lap, and he began spanking my ass. "Ouch!" I tried to get up, but Mark was firm with me, and kept up the spanking. As we struggled, I noticed I was getting very hard. This was kind of kinky, but horny.

Mark grabbed the waistband of my briefs and pulled then down, baring my ass. "You need to learn a lesson that I am the boss, and you will obey me!" He started spanking my bare ass, but I liked that too.

Here we were, two guys the same age, but with his big boxers and my little briefs, we easily slipped into a father/son roleplay. And we both found it very arousing.

"I'm sorry, sir! I won't do it again. I'll do whatever I can to please you!"

"I'm very angry with you, son! It's going to take a lot for you to please me."

"Okay, I'll work hard. I know what you would like. Can I suck your big cock?"

"Yes, that would be a good start."

I got off Mark's lap and kneeled in front of him. I opened the snaps of his boxers and pulled back the material, and his hard cock spilled out. "I'm sorry sir, let me please you."

I took his cock in my mouth and started eagerly sucking on it. His shorts were so loose, I slipped a hand up the leg opening and massaged his balls. I was getting rock hard - this was a very exciting roleplay.

"That feels very good, son. But I think tonight we need to go further. You need to let me fuck you in the ass."


Mark slipped out of the roleplay. "Only if you want to, man. I'll be gentle. I am so hot for you right now. What do you say?"

I thought it over, and agreed to let him try. Neither of us had done that before, but we were so hot for each other, that we wanted something more. Mark stood up, the boxers falling to the floor, and got some Vaseline from the bathroom.

"Okay, boy, on your hands and knees on the bed!"

I climbed up on the bed, my ass in Mark's direction. He smeared some Vaseline on his finger, and slid it in my ass crack and around my asshole. I felt him stand behind me, one hand on my hip, the other guiding his rock hard cock against my hole. He slid his cock across my hole as I spread my cheeks for him. This felt so strange, but I was getting hornier by the minute.

"Okay, son, just relax. This is gonna hurt a bit."

Mark slowly pushed his cock into my asshole until I felt a pop as the head slid in. "Ow, that hurts, man! Take it slow."

"Sorry, try to relax. I'll go very slow."

Luckily, Mark didn't have a very big cock. This would have been a killer with a huge one.

Gradually, I felt him slide further inside, as I tried to relax and make room for him. My cock was iron hard, and throbbing, especially as I felt pressure on my prostate. Mark's hands were on my hips, slowly pulling me on him. "Oh, man, that hurts so good. Fuck me in the ass!"

"Son, your ass is so tight! Tonight, I'll make you a man! Take my cock - all the way!"

I could feel Mark's balls slap against my ass as he started thrusting. I never in a million years thought I would be doing this, but it was so erotic, the pain and pleasure mixed together.

"Fuck my ass, sir! Give me your hot cum!"

After a few more minutes of thrusting, Mark yelled, "Take my cum, boy!", and shot a hot load of sperm in my ass. I could feel the cum spurting in and leaking down my balls and legs. The pressure relaxed as Mark's cock went limp. He reached around and started stroking my hard cock.

"That's a good boy. Now this is for you."

He didn't have to stroke much at all, before I shot a thick load of creamy cum across his sheets. Mark pulled out, and we collapsed into each other's arms on the sticky bed,

"Oh, man, that was so horny. Are you okay?"

"I think so. I'll be a little sore when I sit for a few days. I hope it feels better soon - I want to do this again!"

Mark laughed, "Yeah, me too! Next time you can wear the boxers and be the dad."

"I should have asked my mom to get me some big men's boxers for Christmas instead!"

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